Donald Trump’s 5 Boldest Real Estate Investments and Their Profits
Written by
Sarah Li Cain
Edited by
Rebekah Evans
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Long before his career in politics, President Donald Trump was a wealthy real estate mogul. After taking over his father’s real estate business in 1971, he went on to manage, acquire and sell many types of real estate properties and developments, according to the White House Historical Association. There were of course, real estate flips, some of which were acquired and then sold for a massive profit. Yes, there were losses too.
Here are Trump’s boldest real estate investments.
Grand Hyatt Hotel
In 1976, Trump partnered with Hyatt to acquire the Commodore Hotel in New York City for $10 million for his share, as reported by the New York Times.
The remodel cost around $100 million and lasted around two years, from June 1978 to September 1980. The original renovations had a three story atrium, a glass facade and even a restaurant that was cantilevered over a sidewalk.
In 1996, Trump sold his share to the Hyatt Organization for $140 million for a $130 million profit, per the Baltimore Sun.
Trump International Hotel
This hotel in Washington D.C. opened in 2016 at the city’s old post office building, close to the White House, according to the Guardian. Trump spent around $200 million renovating it into a luxury hotel. In 2021, he sold the leasing rights for a reported $375 million and is now the Waldorf Astoria.
When Trump still owned the property, expected annual revenue was much lower than expected at the $100 million per year. Instead, it only earned around $20 million per year.
Trump Plaza Casino and Hotel
What used to be a skyscraper-like building in Atlantic City, New Jersey is now rubble and an empty lot. After opening in 1984, the casino was one of the most successful in the area. Visitors during that time may have even spotted celebrities like Warren Beatty, Jack Nicholson, Madonna and even Barbara Streisand.
However, things seem to have gone downhill starting in 1991 when Trump decided to build the Trump Taj Mahal casino and poured more money into that building instead. Slowly, the Trump Plaza and Casino fell into disrepair, as there wasn’t much time or attention put into the building. NPR reported the casino closed in 2014 and billionaire Carl Icahn purchased it in 2016. In 2021, the building was demolished.
Spring Creek Towers
Originally called Scarlet City, the property was originally owned by Trump’s father and Trump himself had a 4% state in it after he and his siblings inherited the property. Per AP News, these affordable housing unit buildings earned Trump around $5 million in a year or so, between January 2016 and April 2017.
In 2018, other investors and stakeholders sold the property for $906 million. Trump reportedly earned about $36 million from the sale.
Mar-a-Lago
Trump purchased Mar-a-Lago in 1985, which included the 75,000-square-foot historic mansion on a 16.4-acre estate for a cool $10 million, according to the Miami Herald. While it was initially one of his private residences, Trump converted part of it in 1994 into what’s now called the Mar-a-Lago Club.
Members can stay in guest rooms, use the amenities and a spa onsite. Trump and his family still have his residence in part of the grounds, closed off to others. The club is reported worth $50 million and earned $56.9 million in revenue in 2024, according to Newsweek.
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